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Tear Jerker / Winnie-the-Pooh

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The books

  • The ending of The House at Pooh Corner: Christopher Robin is going away. It's implied he's going to boarding school, which means he won't see his friends again until he's an adult. The characters don't know the specifics, but they band together and write him a goodbye note. As they host a farewell party, Eeyore realizes that the boy wants to be alone with Pooh, and tells the others to leave. Christopher Robin then takes Pooh to 'An Enchanted Place at the Top of the Forest'. They talk together about doing nothing. Christoper Robin mentions that 'they don't let you do nothing. Not for long, anyway.' He tells Pooh of things he'll learn at school—about countries, Kings and Factors, eventually making him his best, most faithful Knight. Then the ending.
    "Pooh, promise you won't forget about me, ever. Not even when I'm a hundred." Pooh thought for a little. "How old shall I be then?" "Ninety-nine." Pooh nodded. "I promise," he said.

    Still with his eyes on the world, Christopher Robin put out a hand and felt for Pooh's Paw. "Pooh," said Christopher Robin earnestly, "if I — if I'm not quite —" he stopped and tried again — "Pooh, whatever happens, you will understand, won't you?"

    "Understand what?" "Oh, nothing." He laughed and jumped to his feet. "Come on!" "Where?" said Pooh. "Anywhere," said Christopher Robin.

    So they went off together. But wherever they go, and whatever happens to them on the way, in that enchanted place on the top of the Forest a little boy and his Bear will always be playing.
    • Surprisingly, the ending was copied almost word for word in the ends of both The Many Adventures of Winnie The Pooh and Pooh's Grand Adventure. Slightly toned down yes, but the implications are still the same-and it's just as sad.

Disney's films

The Many Adventures of Winnie the Pooh

Boo to You Too! Winnie the Pooh

  • Piglet sings a heartbreaking little ditty about how he feels isolated from his friends because of his fearfulness. Later when Pooh empathetically suggests they skip Halloween this year for Piglet, he only feels worse, thinking he's ruined everyone's fun.

Pooh's Grand Adventure

The Tigger Movie

Springtime with Roo

  • Rabbit's Bad Future if he succeeds in making the first day of Spring officially "Spring Cleaning Day". His friends will find him so overbearing and controlling, that they will all move away and leave him alone.
  • The backstory explaining why he's come to hate Easter. After one especially overbearing year as the Easter Bunny, Tigger snuck off with the eggs and the gang went to do hunt them without him. This wasn't what broke Rabbit however. It was how much Roo loved Tigger playing Easter Bunny. He felt rejected since he wanted to make something nice for Roo, but couldn't compete with his Big Brother Worship of Tigger. Also, you can hear the sheer heartbreak coming from Rabbit when he asks how they could celebrate Easter without him, not to mention the sting he felt as a result being left out of the Easter Egg Hunt.
    Rabbit: *solemn* Every Spring...I look forward to one thing most of all; being the Easter Bunny. You took that away from me.
    • The look on Tigger's face upon hearing that sentence. When he heard that, Tigger knew all hope was lost, but he did try to apologize for making Rabbit feel like this anyway. Rabbit, however, wouldn't hear of it and so, Tigger went away dejectedly to tell Roo he wouldn't be getting his Easter Egg Hunt again.
  • Sometime after Tigger's failure to persuade Rabbit to give back Easter to the Hundred Acre Wood, we learn that while Roo was indeed sad over the loss of not getting to enjoy an Easter egg hunt, that was not what bothered him the most. The fact that Roo and the others had unknowingly broken Rabbit's heart since Tigger had outshone Rabbit as the Easter Bunny upset Roo the most. Despite the fact that Rabbit denied the Easter egg hunt, Roo doesn't have the heart to begrudge him for it.
    • When Roo talks to Kanga about how Rabbit felt like he wasn't good enough to be Easter Bunny, you can see it on Rabbit's face that he feels terrible about his actions.

Pooh's Heffalump Movie

  • Lumpy is lost in the forest and trying to get back to his "mummy," but ends up caught in the heffalump trap set by Pooh and the others.
    Lumpy: (to Roo, sobbing) You said they wouldn't be scary.
    Roo: Oh, Lumpy. I'm so sorry. This is all my fault.
    Lumpy: I want my mummy.
  • Poor Eeyore being Demoted to Extra and being forgotten about by the others until the end of the film.
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  • Rabbit and the others tell Roo that he can't go on the heffalump "expotition," (because it's "fraught with danger" and you can't argue with a big word like fraught) which was his idea until Rabbit's Glad I Thought of It and then Kanga starts calling him.
    Kanga: Roo!
    Roo: You mean... I can't go? (ears droop, big frown)
    Rabbit: I'm sorry, Roo.
    Roo: Coming, Mom.

Pooh's Heffalump Halloween Movie

  • Meta example: this film marked the last time John Fiedler voiced Piglet. Fiedler died of cancer three months before the film was released (and only a day after Paul Winchell, Tigger's original actor, also passed away). His death also marked the End of an Era, as Fiedler was the last original member of the voice cast still active in the series.

Winnie-the-Pooh (2011)

  • The trailers, with "Somewhere Only We Know" playing over them. Really hits home for people who have grown up with these stories and are adults now.
    • the lines you can hear most clearly are:
    ...I knew the pathway like the back of my hand...
    ...Is this the place we used to love...?
    ...Oh simple thing, where have you gone...?
  • The look on Pooh's face when his friends gave the jar of honey to the red balloon.
    • And the resulting conversation with Eeyore.
    Pooh: Ever have one of those days where you just can't win?
    Eeyore: I know exactly how you feel.
  • Seeing that almost half the voice actors who worked on previous Pooh productions wouldn't return for this film, including Peter Cullen (Eeyore), Ken Sansom (Rabbit), and Andre Stojka (Owl), the former two in fact were reportedly disappointed they weren't called in for their roles. Especially since Sansom died the following year. Cullen however, was brought back for the Doc McStuffins crossover.
    • One can give respects to Bud Luckey as Eeyore however, who passed away in 2018.
  • A second meta example: this would be the last traditionally animated film in the Disney Animated Canon, and while CGI animation is alright, those who are fond of traditional animation would get a bit emotional.

Christopher Robin

The New Adventures of Winnie the Pooh